P-alkoxybenzilic acids



Patented July 29, 1952 P-AL'KOXYBENZILIC ACIDS Earl R. Bockstahler,Indianapolis, Ind., assignor to Allied Laboratories, Inc., Kansas City,Mo., a corporation of Delaware I N Drawing. Application March 14, 1951,Serial No. 215,657

6 Claims.

The present invention relates to a new class of organic compounds andmore particularly to p-alkoxybenzilic acids and to the processes ofmaking them.

The new compounds of my invention comprise those represented by thefollowing structural formula in which R is an alkyl group having fromfour to eight carbon atoms.

The following specific examples illustrate the preparation of the newcompounds.

EXAMPLE 1 Preparation of dZ-p-n-hexyloxybenzilic acid A solution of 77gm. of p-n-hexyloxybenzil in 800 cc. of ether was mixed with a solutionof 19.8 gm. of potassium hydroxide in 160 cc. of 95% ethanol and allowedto stand for twentyfour hours with occasional shaking. The mixture wasthen shaken with 400 cc. of water. The water layer was separated,filtered, and acidified with hydrochloric acid. After long standing atroom temperature, the oil which precipitated solidified.Recrystallization from petroleum gave a crystalline product which meltedat 62-64 C.

EXAMPLE 2 Preparation of dZ-p-n-butoaybenzilic acid COHCOOH EXAMPLE 3Preparation of dZ-p-n-amoxybenzilic acid A solution of 12 gm. ofp-n-amoxybenzil in 130 cc. of ether was mixed with a solution of 3.2 gm.of potassium hydroxide in 26 cc. of 95% ethanol and allowed to stand fortwenty-four hours with occasional shaking. The mixture was then shakenwith 200 cc. of water. The water layer was separated, filtered, andacidified with 2 hydrochloric acid. After long standing the oil whichprecipitated solidified. Recrystallization from petroleum ether gave acrystalline product which melted at -91 C.

In addition, I have prepared the following compounds utilizing the samemethod illustrated in the specific examples: isobutoxybenzilic acid, M.P. 87-89 C., n-heptyloxybenzilic acid, M. P., 90-91 C., andoctyloxybenzilic acid, M. P., 68-69 C.

The compounds of this invention are useful as intermediates inpreparation of the new therapeutic agents claimed in my co-pendingapplication, Serial No. 87,847, filing date, April 15, 1949, and titledDiethylaminoethyl Alkoxybenzilates, now Patent No. 2,570,181.

The intermediates employed in the present invention can be prepared bythe methods de-' COHCOOH in which R is an alkyl group having from fourto eight carbon atoms.

2. A compound having the structure:

COHGOOH 3. A compound having the structure:

4. A compound having the structure:

OOHCOOH 5. A compound having the structure:

6. A compbund having the structure:

EARL RQBOCKSTAHLER.

OOHCOOH 10 OOHOOOHV REFERENCES CITED The following references are ofrecord in the file of this patent:

1. A COMPOUND HAVING THE STRUCTURE: